By most accounts, Justin Upton has delivered on his promise as a former number-one draft pick and top prospect, hitting 190 home runs and averaging roughly four wins per season since turning 21 years ago. Upton has a rare power-speed combination, he was called up at an early age, he hits for consistent power, and he is still just 28 years old. Yet, not unlike another former first-round pick also hitting free agency, Jason Heyward, Upton is regarded by some as a slight disappointment, if unreasonably so. It is Jason Heyward, with even more youth than Upton to go along with great defense, who is seen as the best position player on the market despite hitting just 13 home runs this past year. Upton’s age, however, should not be dismissed, as he is still younger than most free agents on the market and combines that youth with the promise of considerable power.

Justin Upton will still get paid. Jon Heyman hit a high mark publicly, predicting seven years and $161 million, but FanGraphs crowdsourcing came up with six years, $120 million with Dave Cameron adding an extra year at $20 million to sign with the Yankees. That Upton’s contract is likely to be only the fourth, fifth or perhaps even sixth biggest contract of the offseason speaks to the quality of this free agent class as well as the amount of money that has been added to baseball’s revenues over the past few years.

Six years ago, Matt Holliday signed a seven year, $120 million contract with the St. Louis Cardinals. Since then, nine position players have signed $100 million contracts in free agency and player salaries have increased by 50%. Upton’s six year, $51 million contract served to delay his free agency by two years, but because he debuted at just 19 years old, he is still in position to sign a big long-term contract before the aging process begins his decline.

A trade to San Diego is probably not ideal for any hitter prior to free agency, given the considerable advantages it gives to pitchers. Petco Park opened in 2004, and prior to this season, the season-high for home runs by a right-handed hitter at Petco was 13 by Jedd Gyorko. Will Venable holds the mark for all Padres hitters with 15 home runs at Petco back in 2013. The Padres moved their fences closer in 2013, but the park is still very tough on right-handed hitters, with only the Giants’ and Pirates’ parks suppressing home runs more substantially. Justin Upton managed 15 home runs at home this season, more than any right-handed Padres player has recorded in the last dozen years.

Upton’s future value is tough to gauge. He came up young, and while he did not excel immediately, phenoms might age a bit better than the rest of the population. Speed players, like Upton, have aged better than most players, as well. Upton has used that speed well in the outfield with above range, but he has given back most of that advantage with his subpar arm, making him an average corner outfielder. With the positional adjustment, Upton has been about 50 runs below average in the field. By compensating for that offensively, though, Upton has established himself as a solid three- to four-win player — a good player who could help a lot of teams, but not the star many had once forecast. In his write-up on free agents, Keith Law ranked Upton fourth (behind Heyward, David Price, and Zack Greinke), and he touched on the performance and potential:

He has reached a point in terms of age and experience when it’s irrational to assume he’ll improve in any of these areas, but still rational to price some small probability of improvement into his value. He is simultaneously a good bet to be overpriced by the market, and a nonzero bet to beat his projections by a wide margin.

In trying to find comparable players to Upton, I looked at all outfielders from 1960 to 2008 through age 27 with career WAR totals between 21.5 and 31.5 (Upton’s is 26.5) and PA within 25% of Upton (between 3700 and 6167). I removed the remaining players with a positive defensive value. Then, I kept all hitters with a WAR between two and six in their age-27 seasons (goodbye to Dave Winfield and Vladimir Guerrero). I was left with eight players:

The players above are not a perfect match with Upton. For a bit more perspective, I included another line for Upton which excluded his age-19 and age-20 seasons. Upton is a bit ahead of most of these players defensively while a decent amount behind offensively. Players like Boog Powell, Greg Luzinski, and Jack Clark were not outfielders for very long. This is the difficulty in finding comparables for Upton — he has the power of a lumbering slugger, but the speed of a center fielder. It is also what makes his talent so desirable. Comparisons to players like Strawberry and the chemically enhanced Canseco offer insight into the type of player Upton has been so far, but also presents a murky future. We can take a look at how the players aged to get a decent grasp on the possibilities for Upton. First, looking at the likely good years of the contract in ages 28-31, the group performed fairly well, but did not provide much in the way of excitement.

Justin Upton Comps Through Age 28 to Age 31

Name

PA

wRC+

Off

Def

WAR

Jim Rice

2530

126

74.9

-3.1

15.9

Boog Powell

2155

141

99.7

-32.7

14.4

Jack Clark

1620

157

108

-39.6

12.5

Darryl Strawberry

1506

131

51.4

-7.6

9.9

Jose Canseco

1640

132

68.4

-40.7

8.1

Johnny Callison

2163

110

20.5

-22.7

7.8

Rusty Staub

2263

123

58.6

-66.4

7.2

Greg Luzinski

2090

125

58.4

-69.7

6

AVERAGE

1996

131

67.5

-35.3

10.2

Two-and-a-half wins per season is hardly a bargain when a team is paying $20 million per year, but it is also roughly the going rate on the free agent market. The problem comes when the team is paying for production into the mid-30s and not receiving the same. Here are the Upton comps from age-28 to age-34, a seven-year period.

Justin Upton comps through Age-28 to Age-34

Name

PA

wRC+

Off

Def

WAR

Jim Rice

4290

124

120.7

-23.2

24.6

Jack Clark

3272

153

196.3

-76.2

23.8

Boog Powell

3402

136

135.2

-53.9

20.1

Rusty Staub

4382

121

104.8

-124.7

13.4

Jose Canseco

3246

123

100.0

-86.8

12.0

Darryl Strawberry

1955

126

54.7

-16.7

10.8

Greg Luzinski

3160

121

76.2

-97.1

8.6

Johnny Callison

2938

101

-0.8

-41.3

6.1

AVERAGE

3331

126

98.4

-65.0

14.9

There are three clear successes, and after that, mostly mediocre production. The comps actually go well with Keith Law’s comments above. Pay Upton at the average, and you are more likely than not going to fail to get a positive return, but there is that chance of getting good value still out there. Turning each of the above players’ production as well as the average into dollar terms, here is a graph of the value based on a current $8 million per win with 5% inflation.

An investment in Upton is not one that should be made by a conservative, risk-averse team. Upton’s contract is unlikely to look good at the end of its term, but it does have some upside. Justin Upton’s power is among the best in baseball. Justin Upton is one of only six players to have an isolated slugging percentage above .200 in each of the last three seasons. The other five: Chris Davis, Edwin Encarnacion, Jose Bautista, Mike Trout, and David Ortiz. In the last six offseasons, ten position players have signed free agent contracts in excess of $100 million. Before this offseason, the only player with two seasons left in his 20s was Prince Fielder. Seven of the ten players did not come with a single season before age 30, and only Jose Reyes and Carl Crawford played a single season at age 29 under their new contracts. While Upton’s star does not shine as bright as it did a few years ago, and he has been passed by former teammate Jason Heyward in free agency, his power and youth will get him a significant payday.

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